1-methyl-3-(2-nitrobenzenesulfonyl)imidazol-1-ium triflate | 1555754-86-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-methyl-3-(2-nitrobenzenesulfonyl)imidazol-1-ium triflate
• CAS: 1555754-86-3
• 化学式: CF₃O₃S*C₁₀H₁₀N₃O₄S
• 分子量: 417.344
• InChiKey: OQLJUFCSHJNFNN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  143.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-methyl-3-(2-nitrobenzenesulfonyl)imidazol-1-ium triflate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以69%的产率得到chloro(η⁴-cycloocta-1,5-diene)[1-methyl-3-(2-nitrobenzenesulfonyl)imidazol-2-ylidene]rhodium(I)
  参考文献：
  名称：

  Characterization of Rh(I) complexes bearing N-2-nitrobenzenesulfonyl substituted, N-heterocyclic carbenes

  摘要：

  Synthesis and structural characterization of novel Rh(I) complexes bearing 1,2,4-triazol-3-ylidene or imidazol-2-ylidene substituted with an N-2-nitrobenzenesulfonyl (N-nosyl) group are described. The complexes were characterized by infrared (IR), NMR, and single-crystal X-ray diffraction analyses. The Tolman electronic parameter (TEP) values of both of the 1,2,4-triazol-3-ylidene (2064 cm(-1)) and imidazol-2-ylidene (2059 cm(-1)), as determined from the average carbonyl (CO) stretching frequencies for the corresponding RhCl(NHC)(CO)(2) (NHC = N-heterocyclic carbene) complexes, were higher than that of RhCl(IMes)(CO)(2) (IMes = 1,3-bis(2,4,6-trimethylphenyl) imidazol-2-ylidene) (2050 cm(-1)). As the TEP values of the NHCs increased, the C-13 NMR signal of the carbenic carbon in the corresponding RhCl(NHC)(cod) (cod = 1,5-cyclooctadiene) and RhCl(NHC)(CO)(2) complexes shifted downfield. Moreover, the crystallographic analysis of the RhCl(NHC)(cod) complexes revealed that one of the S=O bonds in the sulfonyl group could be conjugated with the NHC frameworks, while the remaining S=O bond conjugated with the 2-nitrophenyl groups of the N-nosyl substituent. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.12.024
• 作为产物：
  描述：

  邻硝基苯磺酰氯 在 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.75h， 生成 1-methyl-3-(2-nitrobenzenesulfonyl)imidazol-1-ium triflate
  参考文献：
  名称：

  Characterization of Rh(I) complexes bearing N-2-nitrobenzenesulfonyl substituted, N-heterocyclic carbenes

  摘要：

  Synthesis and structural characterization of novel Rh(I) complexes bearing 1,2,4-triazol-3-ylidene or imidazol-2-ylidene substituted with an N-2-nitrobenzenesulfonyl (N-nosyl) group are described. The complexes were characterized by infrared (IR), NMR, and single-crystal X-ray diffraction analyses. The Tolman electronic parameter (TEP) values of both of the 1,2,4-triazol-3-ylidene (2064 cm(-1)) and imidazol-2-ylidene (2059 cm(-1)), as determined from the average carbonyl (CO) stretching frequencies for the corresponding RhCl(NHC)(CO)(2) (NHC = N-heterocyclic carbene) complexes, were higher than that of RhCl(IMes)(CO)(2) (IMes = 1,3-bis(2,4,6-trimethylphenyl) imidazol-2-ylidene) (2050 cm(-1)). As the TEP values of the NHCs increased, the C-13 NMR signal of the carbenic carbon in the corresponding RhCl(NHC)(cod) (cod = 1,5-cyclooctadiene) and RhCl(NHC)(CO)(2) complexes shifted downfield. Moreover, the crystallographic analysis of the RhCl(NHC)(cod) complexes revealed that one of the S=O bonds in the sulfonyl group could be conjugated with the NHC frameworks, while the remaining S=O bond conjugated with the 2-nitrophenyl groups of the N-nosyl substituent. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.12.024